I Helped Create the Milo Trolling Playbook. You Should Stop Playing Right Into It.

OBSERVER — In 2009, I helped sketch out a marketing campaign for an internet personality and blogger named Tucker Max. With a very limited advertising budget available for the independent movie he had written and produced, we had few options for getting the word out.

Maybe it was crazy but my thinking was that one of the best ways to get young men to go see a movie was to tell them they should not be allowed to see it. What ensued was several months of chaos and controversy that ultimately drove Tucker’s book to No. 1 on the New York Times Bestseller list, sold out a multi-college bus tour and ultimately sold millions of dollars worth of tickets, dvds and books.

It was a masterful bit of trolling that admittedly felt a lot more meaningful and exciting when I was younger than it does to me today: We encouraged protests at colleges by sending outraged emails to various activist groups and clubs on campuses where the movie was being screened. We sent fake tips to Gawker, which dutifully ate them up. We created a boycott group on Facebook that acquired thousands of members. We made deliberately offensive ads and ran them on websites where they would be written about by controversy-loving reporters. After I began vandalizing some of our own billboards in Los Angeles, the trend spread across the country, with parties of feminists roving the streets of New York to deface them (with the Village Voice in tow).

But my favorite was the campaign in Chicago—the only major city where we could afford transit advertising. After placing a series of offensive ads on buses and the metro, from my office I alternated between calling in angry complaints to the Chicago CTA and sending angry emails to city officials with reporters cc’d, until ‘under pressure,’ they announced that they would be banning our advertisements and returning our money. Then we put out a press release denouncing this cowardly decision. […]